3 years ago

Biocatalytic Friedel–Crafts Acylation and Fries Reaction

Biocatalytic Friedel–Crafts Acylation and Fries Reaction
Tea Pavkov-Keller, Nina Richter, Wolfgang Kroutil, Karl Gruber, Nina G. Schmidt, Birgit Wiltschi
The Friedel–Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel–Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %, and various C- or O-acyl donors, such as DAPG or isopropenyl acetate, are accepted by this enzyme. Furthermore the enzyme enables a Fries-like rearrangement reaction of resorcinol derivatives. These findings open an avenue for the development of alternative and selective C−C bond formation methods. Order up on Fries: The biocatalytic acylation of resorcinol substrates, catalyzed by an acyltransferase, leads to C-acylated products. The Friedel–Crafts bio-C-acylation allows use of simple activated esters, such as isopropenyl acetate, as an acyl source. Additionally the enzyme enables a Fries-like rearrangement reaction.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201703270

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